ABSTRACT
The chemical investigation of the fresh flowers of Albizia lebbeck (L.) Benth. (Fabaceae, Mimosoideae) led to the isolation of two new echinocystic acid saponins. They were isolated by using chromatographic methods and their structures were elucidated by detailed 1H and 13C NMR spectral data including 2 D-NMR (COSY, HSQC, HMBC and APT) spectroscopic techniques, high-resolution electrospray ionization mass spectrometry (HRESIMS) and acid hydrolysis. Their structures were established as 16-hydroxy-3-[[O-ß-D-xylopyranosyl-(1â2)-O-α-L-arabinopyranosyl-(1â6)-2-(acetylamino)-2-deoxy-ß-D-glucopyranosyl]oxy]-(3ß,16α)-olean-12-en-28-oic acid O-6-deoxy-α-L-mannopyranosyl-(1â4)-O-6-deoxy-α-L-mannopyranosyl-(1â2)-ß-D-glucopyranosyl ester (1) and 16-hydroxy-3-[[O-ß-D-xylopyranosyl-(1â2)-O-α-L-arabinopyranosyl-(1â6)-2-(acetylamino)-2-deoxy-ß-D-glucopyranosyl]oxy]-(3ß,16α)-olean-12-en-28-oic acid 6-O-[(2S,3R,4R)-tetrahydro-3-hydroxy-4-(hydroxymethyl)-2-furanyl]-ß-D-glucopyranosyl ester (2). Additionally, the permeability property and the capacity of interaction with biological membranes of compounds 1 and 2 were investigated.
Subject(s)
Albizzia , Fabaceae , Saponins , Triterpenes , Albizzia/chemistry , Molecular Structure , Triterpenes/chemistry , Saponins/chemistry , FlowersABSTRACT
As part of the ongoing efforts in discovering potentially bioactive natural products from medicinal plants, the present study was conducted to isolate a new complex triterpenoid saponin from the barks of Albizia lebbeck. It was isolated by using chromatographic methods and its structural elucidation was performed using detailed analyses of 1H and 13C NMR spectra including 2D-NMR (COSY, TOCSY, HSQC and HMBC) spectroscopic techniques, high-resolution electrospray ionization mass spectrometry (HRESIMS) analysis and chemical conversions. Its structure was established as 21-[[(2E,6S)-6-[6-deoxy-4-O-[(2E,6S)-6-hydroxy-2-(hydroxymethyl)-6-methyl-1-oxo-2,7-octadienyl]-[(ß-d-glucopyranosyl)oxy]-2-(hydroxymethyl)-6-methyl-1-oxo-2,7-octadienyl]-[(ß-d-glucopyranosyl)oxy]-2,6-dimethyl-1-oxo-2,7-octadienyl]oxy]-16-hydroxy-3-[[O-ß-d-xylopyranosyl-(1â¯ââ¯2)-O-α-l-arabinopyranosyl-(1â¯ââ¯6)-2-(acetylamino)-2-deoxy-ß-d-glucopyranosyl]oxy]-(3ß,16α,21ß)-olean-12-en-28-oic acid O-α-l-arabinofuranosyl-(1â¯ââ¯4)-O-[ß-d-glucopyranosyl-(1â¯ââ¯3)]-O-6-deoxy-α-l-mannopyranosyl-(1â¯ââ¯2)-ß-d-glucopyranosyl ester (1). Additionally, this study aimed to investigate the permeability property of 1, its activity on membrane integrity and supramolecular interactions with cellular constituents using in vitro experimental models.
Subject(s)
Albizzia/chemistry , Cell Membrane/drug effects , Saponins/chemistry , Triterpenes/chemistry , Animals , Erythrocytes/drug effects , Humans , Magnetic Resonance Spectroscopy , Male , Mice , Molecular Structure , Permeability , Saponins/pharmacokinetics , Spectrometry, Mass, Electrospray Ionization , Triterpenes/pharmacokineticsABSTRACT
A new polysaccharide with an estimated weight-average molar mass of 2.6×10(3) was isolated from Allium ampeloprasum var. porrum by hot water extraction, and purified by Sephacryl S-300 HR high-resolution chromatography. It was composed of D-fructose and D-glucose in 10:6 molar ratio, respectively. The structure of the glucofructan was investigated by chemical and spectroscopic methods, including methylation analysis, nuclear magnetic resonance, and electrospray mass spectrometry (ES-MS). The results permitted the structure of the glucofructan to be written as α-D-Glcp-(1â1)-ß-D-Fruf-(2â1)-{[α-D-Glcp-(1â6)-ß-D-Fruf-(2â6)]-ß-D-Fruf-(2â1)}4-ß-D-Fruf-(2â1)-α-D-Glcp. Results of the present study indicated that this new glucofructan exhibited significant gastroprotective property, using in vivo experimental models.
Subject(s)
Cytoprotection/drug effects , Fructans/chemistry , Fructans/pharmacology , Glucose/analogs & derivatives , Stomach/cytology , Stomach/drug effects , Allium , Animals , Carbohydrate Sequence , Glucose/chemistry , Glucose/pharmacology , Male , Mice , Molecular Sequence Data , Molecular WeightABSTRACT
A polysaccharide with an estimated weight-average molar mass of 5.35×10(5) was obtained from an aqueous extract of pseudobulbs of Cyrtopodium andersonii R. Br. It was composed of d-glucose and d-mannose in 1:3 molar ratio. Chemical and spectroscopic analyses revealed a linear structure of the polymer with a backbone composed of (1â4)-linked ß-d-glucopyranosyl and mannopyranosyl units slightly branched at C-2, C-3, and C-6 by side chains, as terminal non reducing residues of d-mannopyranose and d-glucopyranose. It was found to contain 14.6% of acetyl groups substituted at C-2 of (1â4)-linked ß-d-mannopyranosyl units. The acetylated glucomannan demonstrated antiinflammatory and antiulcerogenic activities.
Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/therapeutic use , Anti-Ulcer Agents/therapeutic use , Mannans/chemistry , Mannans/therapeutic use , Orchidaceae/chemistry , Stomach Ulcer/drug therapy , Stomach Ulcer/prevention & control , Acetylation , Animals , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/isolation & purification , Anti-Ulcer Agents/chemistry , Anti-Ulcer Agents/isolation & purification , Carrageenan , Edema/chemically induced , Edema/drug therapy , Ethanol , Male , Mannans/isolation & purification , Mice , Stomach Ulcer/chemically inducedABSTRACT
Many classes of phytochemical products are finding therapeutic use, for example, complex triterpenoid saponins containing in their structures monoterpene moieties. Some of these compounds possess cytotoxic, anti-HIV and adjuvant activities. This review aims to give an overview of these complex triterpenoid saponins with biological activity from the Leguminosae.
Subject(s)
Fabaceae/chemistry , Saponins/chemistry , Saponins/pharmacology , Triterpenes/chemistry , Triterpenes/pharmacology , Molecular StructureABSTRACT
A new steroidal saponin, 3-{(O-6-deoxy-a-L-mannopyranosyl-(1 --> 4)-O-beta-D-glucopyranosyl-(1 --> 3)-O-[O-beta-D-glucopyranosyl-(1 --> 3)-beta-D-glucopyranosyl-(1 --> 2)]-O-beta-D-glucopyranosyl-(1 --> 4)-beta-D-galactopyranosyl)oxy}-6-hydroxy-(3beta,5alpha,6alpha,25R)-spirostan-12-one, was isolated from Agave brittoniana Trel. The structure was determined by extensive NMR spectroscopy studies and chemical conversions. Its effects on the Na+-ATPase and (Na+ + K+)-ATPase activities of the proximal tubule from pig kidney were evaluated. It was observed that this steroidal saponin exerts a biphasic effect on the Na+-ATPase activity. It is concluded that the effect of the aqueous extract as a diuretic is due, at least in part, to the action of saponin on the ouabain-insensitive Na+-ATPase.
Subject(s)
Agave/chemistry , Saponins/chemistry , Saponins/pharmacology , Sodium-Potassium-Exchanging ATPase/metabolism , Steroids/chemistry , Steroids/pharmacology , Animals , Carbohydrate Conformation , Carbohydrate Sequence , Cell Membrane/enzymology , Kidney Tubules/enzymology , Kinetics , Methylation , Models, Molecular , Molecular Sequence Data , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Plant Extracts/pharmacology , Plant Leaves/chemistry , Saponins/isolation & purification , Sodium/pharmacology , Sodium-Potassium-Exchanging ATPase/drug effects , Steroids/isolation & purification , SwineABSTRACT
Two new steroidal saponins were isolated from the rhizomes of Costus spiralis Rosc. Their structures were established as (3beta,25R)-26-(beta-D-glucopyranosyloxy)-22-hydroxyfurost-5-en-3-yl O-D-apio-beta-D-furanosyl-(1-->2)-O-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyranoside (1) and (3beta,25R)-26-(beta-D-glucopyranosyloxy)-22-hydroxyfurost-5-en-3-yl O-D-apio-beta-D-furanosyl-(1-->4)-O-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyranoside (2). Their structural identifications were performed using detailed analyses of 1H and 13C NMR spectra including 2D NMR spectroscopic techniques (DEPT, COSY, HETCOR and COLOC) and chemical conversions. The steroidal saponins were evaluated for anti-inflammatory activity.
Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Costus/chemistry , Saponins/chemistry , Saponins/pharmacology , Steroids/chemistry , Steroids/pharmacology , Animals , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/isolation & purification , Magnetic Resonance Spectroscopy , Male , Mice , Mice, Inbred BALB C , Models, Molecular , Molecular Conformation , Plant Leaves/chemistry , Saponins/isolation & purification , Steroids/isolation & purificationABSTRACT
A polysaccharide, an alpha-D-glucan with an apparent molecular weight of 6.85 x 10(4), called PSa glucan, was isolated from fresh seeds of Sorghum arundinaceum by fractionation on Sephacryl S-300 HR and Sephadex G-25. Chemical and spectroscopic studies indicated that it has a highly branched glucan type structure composed of alpha-(1-->4) linked D-glucopyranose residues with (1-->3), (1-->6) branching points, and a significant amount of alpha-(1-->6) branching to alpha-(1-->3) linked D-glucopyranose residues. The anti-inflammatory activity of the polysaccharide was performed using the capillary permeability assay.
Subject(s)
Anti-Inflammatory Agents/chemistry , Edible Grain/chemistry , Polysaccharides/chemistry , Seeds/chemistry , Animals , Anti-Inflammatory Agents/pharmacology , Carbohydrate Conformation , Carbohydrate Sequence , Gas Chromatography-Mass Spectrometry , Male , Methylation , Mice , Mice, Inbred BALB C , Molecular Sequence Data , Oligosaccharides/chemistry , Oligosaccharides/isolation & purification , Plant Extracts/chemistry , Polysaccharides/isolation & purification , Polysaccharides/pharmacology , SteroidsABSTRACT
A new steroidal saponin was isolated from the leaves of Agave attenuata Salm-Dyck. Its structure was established as (3beta,5beta,22alpha,25S)-26-(beta-D-glucopyranosyloxy)-22-methoxyfurostan-3-yl O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-glucopyranosyl-(1-->3)]-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside. The structural identification was performed using detailed analyses of 1H and 13C NMR spectra including 2D NMR spectroscopic techniques (COSY, HETCOR and COLOC) and chemical conversions. The haemolytic potential of the steroidal saponin was evaluated and the anti-inflammatory activity was performed using the capillary permeability assay.
Subject(s)
Agave/chemistry , Phytosterols/chemistry , Plant Extracts/chemistry , Saponins/chemistry , Carbohydrate Conformation , Carbohydrate Sequence , Molecular Sequence Data , Molecular Structure , Oligosaccharides/chemistry , Oligosaccharides/isolation & purification , Phytosterols/isolation & purification , Plant Leaves/chemistry , Saponins/isolation & purificationABSTRACT
An arabinogalactan with mean Mr of 6.85 x 10(4), was isolated from the pulps of Melocactus depressus Hook by fractionation on Sephacryl S-300 HR. Chemical and spectroscopic studies indicated that it has a branched arabinogalactan type structure composed of beta-(1-->4) linked D-galactopyranose residues with beta-(1-->3) and beta-(1-->6) branching points. Its structural features include also alpha-(1-->2), alpha-(1-->3) and alpha-(1-->5) linked L-arabinofuranose residues. The polysaccharide demonstrated a phagocytosis stimulating property.